San Jose (SJC) to Chicago (ORD), Jan 19–26, 2027: from $363 round trip

San Jose (SJC) to Chicago (ORD), Jan 19–26, 2027: from $363 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $363 round trip, Axel-exclusive, Alaska Airlines / American Airlines, 1 stop, Jan 19–26, 2027, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Jan 19–26, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

All hotels in Chicago

Route overview: San Francisco Bay Area to Chicago (ORD) flight deals

2027-01-19 → 2027-01-26 · Axel-exclusive $363.38

• Alaska Airlines AS653 / AS1478: SJC 2027-01-19 09:54:00 → ORD 2027-01-19 19:00:00; 1 stop(s) via SAN; 426 minutes. Local airport times.
  • AS653: SJC 2027-01-19 09:54:00 → SAN 2027-01-19 11:19:00; layover at SAN: 83 minutes.
  • AS1478: SAN 2027-01-19 12:42:00 → ORD 2027-01-19 19:00:00.
• American Airlines AA834 / AA3113: ORD 2027-01-26 13:26:00 → SJC 2027-01-26 18:34:00; 1 stop(s) via PHX; 428 minutes. Local airport times.
  • AA834: ORD 2027-01-26 13:26:00 → PHX 2027-01-26 16:21:00; layover at PHX: 74 minutes.
  • AA3113: PHX 2027-01-26 17:35:00 → SJC 2027-01-26 18:34:00.

2027-01-19 → 2027-01-26 · Axel-exclusive $370.50

• American Airlines AA3257 / AA1528: SJC 2027-01-19 13:05:00 → ORD 2027-01-19 21:58:00; 1 stop(s) via PHX; 413 minutes. Local airport times.
  • AA3257: SJC 2027-01-19 13:05:00 → PHX 2027-01-19 16:05:00; layover at PHX: 81 minutes.
  • AA1528: PHX 2027-01-19 17:26:00 → ORD 2027-01-19 21:58:00.
• American Airlines AA834 / AA3113: ORD 2027-01-26 13:26:00 → SJC 2027-01-26 18:34:00; 1 stop(s) via PHX; 428 minutes. Local airport times.
  • AA834: ORD 2027-01-26 13:26:00 → PHX 2027-01-26 16:21:00; layover at PHX: 74 minutes.
  • AA3113: PHX 2027-01-26 17:35:00 → SJC 2027-01-26 18:34:00.

2027-01-19 → 2027-01-26 · Axel-exclusive $370.50

• United Airlines UA2013 / UA1651: SJC 2027-01-19 08:45:00 → ORD 2027-01-19 18:38:00; 1 stop(s) via DEN; 473 minutes. Local airport times.
  • UA2013: SJC 2027-01-19 08:45:00 → DEN 2027-01-19 12:20:00; layover at DEN: 161 minutes.
  • UA1651: DEN 2027-01-19 15:01:00 → ORD 2027-01-19 18:38:00.
• United Airlines UA2495 / UA1256: ORD 2027-01-26 08:40:00 → SJC 2027-01-26 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2027-01-26 08:40:00 → DEN 2027-01-26 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2027-01-26 11:35:00 → SJC 2027-01-26 13:18:00.

2027-01-19 → 2027-01-26 · Axel-exclusive $389.50

• Delta Air Lines DL1254 / DL2413: SJC 2027-01-19 13:39:00 → ORD 2027-01-19 22:27:00; 1 stop(s) via SLC; 408 minutes. Local airport times.
  • DL1254: SJC 2027-01-19 13:39:00 → SLC 2027-01-19 16:40:00; layover at SLC: 95 minutes.
  • DL2413: SLC 2027-01-19 18:15:00 → ORD 2027-01-19 22:27:00.
• Delta Air Lines DL756 / DL3883: ORD 2027-01-26 14:25:00 → SJC 2027-01-26 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2027-01-26 14:25:00 → LAX 2027-01-26 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2027-01-26 18:05:00 → SJC 2027-01-26 19:25:00.

2027-01-19 → 2027-01-26 · Axel-exclusive $389.50

• Delta Air Lines DL2904 / DL1178: SJC 2027-01-19 22:40:00 → ORD 2027-01-20 08:34:00; 1 stop(s) via ATL; 474 minutes. Local airport times.
  • DL2904: SJC 2027-01-19 22:40:00 → ATL 2027-01-20 06:10:00; layover at ATL: 75 minutes.
  • DL1178: ATL 2027-01-20 07:25:00 → ORD 2027-01-20 08:34:00.
• Delta Air Lines DL756 / DL3883: ORD 2027-01-26 14:25:00 → SJC 2027-01-26 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2027-01-26 14:25:00 → LAX 2027-01-26 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2027-01-26 18:05:00 → SJC 2027-01-26 19:25:00.

2027-01-19 → 2027-01-26 · Axel-exclusive $396.63

• United Airlines UA2004: SJC 2027-01-19 14:14:00 → ORD 2027-01-19 20:32:00; nonstop; 258 minutes. Local airport times.
• United Airlines UA2495 / UA1256: ORD 2027-01-26 08:40:00 → SJC 2027-01-26 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2027-01-26 08:40:00 → DEN 2027-01-26 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2027-01-26 11:35:00 → SJC 2027-01-26 13:18:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Jan 18, 2027 · Return options
• Jan 20, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Jose (SJC) to Chicago (ORD) · Jan 19, 2027 · return Jan 26, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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